2-{[(1S,10R,11S,13R,14R,15S)-13,14-dihydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl]oxy}acetic acid

• ChemBase ID: 131077
• Molecular Formular: C20H26O5
• Molecular Mass: 346.41744
• Monoisotopic Mass: 346.17802393
• SMILES: C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1C[C@H]([C@@H]2O)O)OCC(=O)O
• Canonical SMILES: OC(=O)COc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H]([C@@H]2O)O)C
• InChI: InChI=1S/C20H26O5/c1-20-7-6-14-13-5-3-12(25-10-18(22)23)8-11(13)2-4-15(14)16(20)9-17(21)19(20)24/h3,5,8,14-17,19,21,24H,2,4,6-7,9-10H2,1H3,(H,22,23)/t14-,15-,16+,17-,19+,20+/m1/s1
• InChIKey: SZBWYTRVLQFZGU-UQZPWQSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(1S,10R,11S,13R,14R,15S)-13,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}acetic acid
• IUPAC Traditional name: {[(1S,10R,11S,13R,14R,15S)-13,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}acetic acid
• Synonyms: 1,3,5-(10)-Estratriene-3,16α,17β-triol 3-carboxymethyl ether; Estriol 3-carboxymethyl ether

Database IDs

• CAS Number: 69260-14-6
• MDL Number: MFCD00079175
• PubChem SID: 24894463; 162225355
• PubChem CID: 16219311

CALCULATED PROPERTIES

• Acid pKa: 3.7795498
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.5725258
• LogD (pH = 7.4): -0.9771799
• Log P: 2.294475
• Molar Refractivity: 91.8331 cm^3
• Polarizability: 36.2233 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

DETAILS

Sigma Aldrich - E2262

Application
Estriol 3-carboxymethyl ether was coupled to BSA and used as immunogen for raising anti-estriol immunoglobulins.1